Identify compounds A-I in the following synthesis scheme. CUCN D conc HNO3 1. HCI, Fe NaNO2 A 2. NaOH В HCI Same as above Br2 Mg(s). F Et,0 1. D NaBH4 1. NaH >E FeBr3 G ELOH 2. H2О (еxcess), H,SO4 2. C6H5CH,Br

Identify compounds A-I in the following synthesis scheme. CUCN D conc HNO3 1. HCI, Fe NaNO2 A 2. NaOH В HCI Same as above Br2 Mg(s). F Et,0 1. D NaBH4 1. NaH >E FeBr3 G ELOH 2. H2О (еxcess), H,SO4 2. C6H5CH,Br

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter8: Addition Via Carbocation

Section: Chapter Questions

Problem 21CTQ

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Question

Identify compounds A-I in the following synthesis scheme.
CUCN
D
conc HNO3
1. HCI, Fe
NaNO2
A
2. NaOH
В
HCI
Same as above
Br2
Mg(s).
F
Et,0
1. D
NaBH4
1. NaH
>E
FeBr3
G
ELOH
2. H2О (еxcess), H,SO4
2. C6H5CH,Br

Expert Solution

Step 1

1) Conc. HNO3 is the source of nitronium ion. Hence it is used to form nitro products.

2) Diazotisation: The process of formation of diazonium salts is called diazotisation.

3) Sandmeyer Reaction: The Cl^-, Br^-, and CN^- nucleophiles can be easily introduced in the benzene ring in the presence of copper ion.

4) Reaction of Halide with magnesium in the presence of ether results in the formation of Grignard reagent. Grignard reagent further reacts with carbonyl or nitriles to form alcohols are ketones respectively.

5) NaBH₄: Sodium borohydride. It is the reducing agent used to reduce ketones selectively to alcohols.

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